1-[4-[(2S,3R,4S,5S,6R)-6-[[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-methoxyphenyl]ethanone

Details

• Internal ID: 28bab72c-d609-4606-b585-0be719b580f3
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[4-[(2S,3R,4S,5S,6R)-6-[[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-methoxyphenyl]ethanone
• SMILES (Canonical): CC(=O)C1=CC(=C(C=C1)OC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O)OC
• SMILES (Isomeric): CC(=O)C1=CC(=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@@H]3[C@H]([C@@](CO3)(CO)O)O)O)O)O)OC
• InChI: InChI=1S/C20H28O12/c1-9(22)10-3-4-11(12(5-10)28-2)31-18-16(25)15(24)14(23)13(32-18)6-29-19-17(26)20(27,7-21)8-30-19/h3-5,13-19,21,23-27H,6-8H2,1-2H3/t13-,14-,15+,16-,17-,18-,19+,20+/m1/s1
• InChI Key: MKRWWSNBWNFVDX-WYZVAZFISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₁₂
• Molecular Weight: 460.40 g/mol
• Exact Mass: 460.15807632 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.46
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6373	63.73%
Caco-2	-	0.8518	85.18%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7185	71.85%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9217	92.17%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5767	57.67%
P-glycoprotein inhibitior	-	0.6679	66.79%
P-glycoprotein substrate	-	0.5779	57.79%
CYP3A4 substrate	+	0.6252	62.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8484	84.84%
CYP3A4 inhibition	-	0.8643	86.43%
CYP2C9 inhibition	-	0.8995	89.95%
CYP2C19 inhibition	-	0.8725	87.25%
CYP2D6 inhibition	-	0.9146	91.46%
CYP1A2 inhibition	-	0.8826	88.26%
CYP2C8 inhibition	+	0.6617	66.17%
CYP inhibitory promiscuity	-	0.8401	84.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6440	64.40%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.8288	82.88%
Skin corrosion	-	0.9542	95.42%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4148	41.48%
Micronuclear	-	0.6126	61.26%
Hepatotoxicity	-	0.7083	70.83%
skin sensitisation	-	0.8353	83.53%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.6610	66.10%
Acute Oral Toxicity (c)	III	0.6940	69.40%
Estrogen receptor binding	+	0.7520	75.20%
Androgen receptor binding	-	0.6675	66.75%
Thyroid receptor binding	+	0.5559	55.59%
Glucocorticoid receptor binding	-	0.5423	54.23%
Aromatase binding	+	0.5934	59.34%
PPAR gamma	+	0.6046	60.46%
Honey bee toxicity	-	0.8719	87.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7366	73.66%
Fish aquatic toxicity	-	0.4321	43.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.55%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.42%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.05%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.69%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	90.68%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.45%	94.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.64%	97.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.41%	96.00%
CHEMBL4208	P20618	Proteasome component C5	88.90%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.03%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.86%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.70%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.52%	95.56%
CHEMBL2535	P11166	Glucose transporter	83.63%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	83.55%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.45%	97.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.77%	96.90%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.65%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.68%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.82%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.60%	94.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.44%	95.83%

Plants that contains it

• Sargentodoxa cuneata

Cross-Links

• PubChem: 163188526
• LOTUS: LTS0157457
• wikiData: Q105166183